DURING THIS FUNDING PERIOD WE HAVE BEEN INVESTIGATING THE ALKYLATION OF CHIRAL GLYCINE EQUIVALENTS FOR THE SYNTHESIS OF LABELED AMINO ACIDS. IN PARTICULAR, WE HAVE USED THE CAMPHOR-BASED CHIRAL GLYCINE ORIGINALLY DESCRIBED BY OPPOLZER AND COWORKERS (SCHEME 1). OPPOLZER'S CHIRAL AUXILIARY CONTAINS A SULTAM RING FUSED TO THE CAMPHOR NUCLEUS; N-PROTECTED GLYCINE (N-(BISMETHYLTHIO)-METHYLENE GLYCINE) IS LINKED TO AS AN AMIDE TO THE NITROGEN IN THE SULTAM RING. THE CAMPHOR GLYCINATE IS TREATED WITH AN EQUIVALENT OF N-BUTYL LITHIUM TO YIELD THE CORRESPONDING GLYCINE ENOLATE. ALKYLATION OF THE ENOLATE OCCURS BY TREATMENT WITH THE APPROPRIATE ALKYL IODIDE TO YIELD THE BLOCKED AMINO ACID. THE BLOCKING GROUPS ARE REMOVE IN TWO STEPS TO YIELD L-AMINO ACIDS. THE OVERALL PROCESS OCCURS WITH REMARKABLE STEREOSELECTIVITY YIELDING AMINO ACIDS IN THE DESIRED L-CONFIGURATION IN ENANATIOMERIC EXCESS OF >98%. PREVIOUSLY, WE ESTABLISHED THIS CHEMISTRY IN OUR LABORATORY AND OPTIMIZED OPPOLZER'S REACTION CONDITIONS FOR LABELING BY ALKYLATING WITH A SERIES OF ALKYL IODIDES INCLUDING METHYL IODIDE (L-ALANINE), ISOPROPYL IODIDE (L-VALINE), 1-IODO-2-METHYL PROPANE (L-LEUCINE), AND BENZYL IODIDE (L-PHENYLALANINE. USING THIS GENERAL APPROACH WE HAVE PRODUCED A VARIETY OF 13C, 15N, AND 2H ISOTOPOMERS OF L-ALANINE, L-VALINE, L-LEUCINE, AND L-PHENYLALANINE. USING AN APPROPRIATE ALKYLATING AGENT AND THIS REACTION SCHEME, IT IS POSSIBLE TO THINK OF APPROACHES TO THE STEREOSELECTIVE SYNTHESIS OF ALL NINETEEN OF THE CHIRAL AMINO ACIDS. THIS YEAR WE EXAMINED A VARIETY OF USEFUL ALKYLATING AGENTS THAT YIELD OTHER COMMON AMINO ACIDS INCLUDING PROLINE, ASPARAGINE, ASPARTIC ACID, LYSINE, AND SERINE. MUCH OF THIS WORK IS DETAILED IN THE HIGHLIGHTS SECTION OF THIS PROPOSAL.